4-(4-Fluorobenzoyl)piperidine → HCID 66626278, compound

HRID 1664961Notes

Reaction equation

HRID 1664961 reaction equation
[F:1][C:2]1[CH:15]=[CH:14][C:5]([C:6]([CH:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[O:7])=[CH:4][CH:3]=1.[C:16]([O:20][C:21](=[O:29])[NH:22][CH2:23][C@@H:24]1[CH2:26][C@H:25]1[CH:27]=O)([CH3:19])([CH3:18])[CH3:17].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[C:16]([O:20][C:21](=[O:29])[NH:22][CH2:23][C@@H:24]1[CH2:26][C@H:25]1[CH2:27][N:11]1[CH2:12][CH2:13][CH:8]([C:6](=[O:7])[C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:15][CH:14]=2)[CH2:9][CH2:10]1)([CH3:19])([CH3:17])[CH3:18]

Participants

5

Reactant 3

HCID 27244404-(4-Fluorobenzoyl)piperidineHCID 5049666Sodium triacetoxyborohydrideHCID 45091916HCID 45091916, compound

Product 1

HCID 66626278HCID 66626278, compoundYield 61.7%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of 4-(4-fluorobenzoyl)piperidine (0.300 g, 1.2 mmol), Trans-(2-Formyl-cyclopropylmethyl)-carbamic acid tert-butyl ester (0.294 g, 1.2 mmol), in 1, 2 dichloroethane (2 mL) was stirred for 4 h at room temperature and sodium triacetoxyborohydride (0.470 g, 2.2 mmol) was added and the resulting solution was stirred for 12 hours until the TLC indicated completion of the reaction. The mixture was filtrated and concentrated to dryness and purified with column chromatography on silica gel using CH2Cl2—CH2Cl2/MeOH (1-9:1). The product fractions were concentrated to give 0.288 g (0.74 mmol, 60% yield) of a white solid. MS (m/e): 391.3 (M+H+).

Workup

  1. customcompletion of the reaction
  2. filtrationThe mixture was filtrated
  3. concentrationconcentrated to dryness
  4. custompurified with column chromatography on silica gel
  5. concentrationThe product fractions were concentrated

Sources & evidence

ORD record
ord-9c9ff9f29c6141749b3f29b83a2208d6
Source dataset
uspto-grants-2011_10
Patent number
US08039490B2

Reaction notes

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